Cruel Intentions
by timewasting101
Summary: Based on the Film Cruel Intentions: AU from the series. A teenage world where love is nothing but a game, but games always get too close for comfort. (Derena pairing but I will attempt to include the other characters and make it more well rounded)
1. Chapter 1

St Jude's and Constance Billard had a status quo like all other schools. The jocks could often be found throwing balls around or discussing their most recent conquests; the girls would be grouped in the cliques gossiping about one another; it was a guarantee that there would be stoners getting high openly in the middle of the courtyard, knowing if they were to be told off a sizeable donation from their family would have the stain removed from their academic record. But, this day was different. The junior from Brooklyn could hardly believe his eyes when he entered the school gates after lunch and saw every child engrossed in some sort of magazine. With a closer look he noticed it was the student school magazine, which was even more baffling considering it was normally allowed to collect dust in the library. He soon began to notice that gradually more and more people were beginning to stare at him which only further put him at edge.

Seeking out his mate Carter in crowd he asked, "You want to tell what has got everything acting so weird?"

With a sombre look on his face Carter handed him the magazine, already turned to a particular article titled _'The Cruel Intentions of the Upper East Side'_.

"You need to read this" Carter replied, holding Dan's gaze until he finally took the paper from his grasp.

_Ever since grade school there have been two girls who pretty much run the Upper East Side, Serena van der Woodsen and Blair Waldorf. Girls flock to them, just waiting and hoping for that glance of approval. As for the male attention, the reasoning is quite simple, they are beautiful._

_Blair, epitomises class. Her outfits are always well put-together, at times suggestive but never too revealing. And, with her perfect grades and relentless ambition she is loved by the teachers. But, to everyone else there is only one way to describe her, 'Bitch'. However, she owns it, and one can't help but admire and respect her ability to destroy self esteem anywhere and everywhere. All it takes is a withering glare or a cutting remark._

_As for Serena, she's the girl that everyone falls for. I should know, I've been in love with her for as far back as I can remember. She's tall, blonde and beautiful, with such a care-free attitude that no matter what kind of day you've had, her presence can always illicit a smile. When she walks into a room she doesn't command attention with the authority that Blair has naturally, but nonetheless people are drawn to her._

_They are the yin to each other's yang, and when you see them together, they are definitely a sight to behold. It's not hard to understand why people can't help love them, whilst also loving to hate them._

_However, there is more too them than what everyone sees. I should know, I've been best friends with them my whole life. Blair and I have been a couple since the sandpit, and like I've already said, Serena captured my heart just as early on. I'm guessing you've all worked out by now who's writing this, but I'll still confirm it anyway. Yes, you are correct, this is me, Nate Archibald. However, I too am more than what you all see. I'm not just the dumb jock/golden boy that everyone assumes I am. Or at least, I'm not anymore. One could say I've had my eyes opened this year, and I guess the reason I'm writing this is to open yours too._

_Blair is more than just a bitch, more than just an excellent student and self-confessed expert schemer. She's insecure, just like most other teenagers, myself included. Her mother is a fashion designer who always strives to achieve perfection in her looks, and her best-friend manages to effortless reach those ideals. So Blair nitpicks at herself and puts other down as a means of keeping herself on top. Her father, left her family for a male model and she now barely see the man she used to idolise. She has so many issues, just like everyone else, and she is far from the model of perfection that you all see, but still light-years above the broken girl she sees herself as. She can be warm, kind and funny if you are one of the lucky few who truly get to know her. Plus, she would go to the ends of the Earth for her friends, although I'm guessing after this I'm most likely no longer one of them. I just hope that, at some point, she feels comfortable enough to let everyone see the real her._

_Serena, too has her fair share of insecurities. Her father left before she could develop clear memories of him and her mother has proceeded to become a serial divorcee. Nothing in her life is stable, so she found solace in alcohol, drugs and boys. However she still smiles every day, and manages to not let it bring her down. It would be inspiring if there wasn't another side to her that most of you don't get to see. _

_You all think that Blair is the bitch, but at least with her you know what you are in for. There is a darker side to Serena, a manipulative side that is worse because it sneaks up on you unsuspectingly. It even sneaks up on her. And, because all she does is block out all of her other problems, it is easy for her to forget about it, and not care about the hearts she breaks and the damage that she herself can cause. Then we all ignore it because of the sunny exterior she exudes. This year, that side became more apparent to me. This year I saw Serena toy with someone's heart as part of a game of revenge, and he still has no clue it is even happening. _

_You want to know what this article is about? To sum up. This article is about the truth. This article is about revealing who your elite really are. This article is about how I was forced to take a long hard look at the people I am surrounded by and the small bubble we live in._


	2. Chapter 2

Note: The story now goes back in time, detailing the events leading up to the 1st Chapter.

_It all began the night of Josh's party . . ._

"Oh my God, Blair you look so hot in that dress"

"Do you think Nate will like it." Blair said twisting to get a good look in the mirror at the tight black dress she was currently wearing, "I feel like he's been pulling away recently."

At this Serena could only go back to re-examining the jewellery in Blair's box. Nate had been staring at her quite often recently, he'd tried to be subtle and do it when he thought she wasn't watching, but she'd definitely caught him a few times. She couldn't help but be flattered by the attention. Her and Natie had always had a bit of a connection. They were the lost souls of their little foursome. Blair and Chuck were the experts at scheming and tended to take life a little too seriously, always having some kind of goal or takedown up their sleeves, whereas she and Nate could always just have fun.

However, he was off limits, and she knew that. Blair had laid her claim on him the first time they'd all met. The two had been together ever since. They were Upper East Side's answer to a Will and Kate, ready to take the throne after uniting the Vanderbilt and Waldorf line. On paper they were perfect together, and Serena knew that her best friend saw Nate as her forever, but somehow she couldn't help herself but consider an alternative future, one where she got the happy ending.

"C'mon, you know Nate. The vacant stare is just his thing, I think he and Chuck just got a new batch of weed from that guy up at Clarence House," Serena replied attempting to alleviate Blair's concerns.

"Hmm, I remember them talking about it," Blair continued to examine herself running her hands down her sides to the hemline of her dress, "You're probably right, but I still don't think I can pull this off. I don't have the legs for it.".

Looking over at Serena, Blair could only envy the ease with which Serena was able to pick and choose her clothes. Everything looked fantastic on her, with her golden hair and legs that she had many heard guys say 'went on forever', in their awe-struck tones. As much as she would hate to be leered over by the male population, it was a fact of life that all girls need to know whether or not they are attractive. She was no exception. It certainly didn't help that even her own boyfriend was at times clearly entranced by her best friend. Blair could only be thankful that Serena was so pre-occupied by the rest of her male suitors to notice.

"No way, your legs are fantastic. Now go put on the Louboutin's I pulled out and I guarantee you'll have him eating out of the palm of your hand," Serena then turned to Blair and with a cheeky grin continued, "or any other place you want," aiming to make the conversation more light hearted.

Laughing Blair, grabbed a pillow and launched it at the now laughing blonde, "You have such a dirty mind,"

"Yeah, but, you love me anyway," Serena replied as she whipped out a flask to hand over to Blair, "especially considering I brought some of Chuck's finest."

"Why do I get the feeling that tonight is going to be mess," Blair said with a slight smile.

"You say messy, I say fantastic."Walking over to Blair, Serena put the flask in Blair's hand, "It's the last big party before Ivy Week and you promised you'd let your hair down this once."

Watching the smile grow on Serena's face, Blair began to drink.

Dan could only stare at little sister in disbelief as she scanned to room for her phone, preparing to go out, "I can't believe you are actually going to this party."

Jenny smirked at him, "You're just jealous that I'm invited and you're not."

Laughing Dan rose from his seat on the couch to hand pick up the missing device from beside the lamp, "Of course I am. I just wish that I was in your position, waiting hand and foot for girls like Blair Waldorf so I could attain such an honour as going to Josh Whitman's first party of the year," he said sarcastically, handing the phone over, "Is this what you're looking for?"

"Yeah, well, you wouldn't be complaining if it was Serena would you? Anyway, just because you live your high school life on the sidelines doesn't mean I have to." Jenny replied, as she grabbed her bag off the counter to put her phone in, "and thank you."

"Hey, it's a choice," Dan said choosing to ignore the Serena jibe, because let's be honest, he would happily serve her every whim if she asked him to. Unfortunately, she had no idea who he was, so even a discussion was off the cards. "I just don't get why you want to be her friend so much. She's only ever going to see you as the scholarship kid from Brooklyn. Trust funds and family legacies are the only things people like her respect, and I hate to break it to you, but we Humphreys have neither."

Looking at Dan exasperatedly, Jenny couldn't help but get annoyed at her brother's often repeated rant about their schoolmates. Even though she knew his heart was in the right place, she didn't think he was right. Whilst the Constance girls' had been a bit catty towards her, she knew that eventually she could earn their respect on her own terms, regardless of her family's lack of wealth. It wasn't about money, it was about proving you had power and the first step was to get in with Blair Waldorf. She just needed to show that she could handle anything thrown her way, and Jenny was right on her way to doing that.

"How many times do we have to have this conversation. I don't think they are all that shallow," however at Dan's sceptical look she did concede a bit, "Ok, most of them are, but not all of them. Anyway, I am running late and I think my cab's arrived so I've got to go." Jenny picked up her bag and jacket and made a move to the front door.

"Did you write, down the address of the place like Dad said?" Dan asked.

"Yep, it's on the counter. And I'll remember to text you when I arrive and when I'm about to leave," Jenny said, and she couldn't help but roll her eyes at her dad and brother's protective streak kicking in.

"Alright then," Dan nodded, as she opened the door, but then he called her back just as she was about to leave.

"Hey, hold on a sec," he said as she came back in. He couldn't help but be a little worried for his sister. He knew she was growing up, and if he hadn't before, the dress she was wearing plus the make-up definitely clued him in/ However, he still didn't think she knew what she was getting into with these girls and their parties. He'd heard many a story of the antics that would go on behind the closed doors of the seemingly mature and intelligent kids of Constance and St. Jude's, and he didn't want his sister to lose herself in all their drama. Where all the other kids had money, prestige and influence to fall back on, Jenny didn't. However, at the same time, it had been a while since he had seen her this excited and he didn't want to take that away from her.

"Just be careful. Have fun, but, please be careful too." Dan said sincerely.

Recognising the shift to a more serious tone from her brother Jenny responded similarly, "Trust me. I know what I'm doing. I'll be ok. I promise."

At this Dan nodded once again and watched as his sister walked out the door on her way to attend her first ever Upper East Side party.

Nate looked out over the edge of the balcony as he listened to Chuck bragging about his latest conquest, Emily Rogers, a hot senior who was also a strict Catholic and head of the chastity club for Constance. Supposedly she was quite the screamer.

He couldn't help but be jealous of his best friend. Chuck was able to do and get everything wanted and never had to think twice about the repercussions for his families like Nate had to. The 'precious' reputation of the Vanderbilt line was always on his mind and dictated his actions. Admittedly, it did suck for the Bass boy that he had an absentee father, but at least he was able to make his own choices, even if they did include persuading girls to break their promises to God.

Nate had been in a relationship with Blair for as long as he could remember. He'd always cared for her, but he knew in his heart that he didn't love the way he was supposed to. Especially at this stage in their relationship, considering the hints his mother had been dropping regarding the Vanderbilt ring. If he was truly honest with himself, he knew there had always been something holding him back from truly committing to the Waldorf heir . . . or someone to be more precise. Serena Van der Woodsen had always been able to capture his attention, from that first day in the playground when she'd wildly marched up to him demanding he go and talk to her best friend, the more quiet and composed brunette sitting on the swing she'd already claimed as her throne. For some reason, he'd never be able to get her out of his head, and it was about more than just her beauty. He didn't know whether to describe as careless of carefree, but one way or another, when he was around her he felt like he too could do or be anything he wanted.

A wolf whistle snapped Nate out of his thoughts, causing him to turn to Chuck in confusion.

"What was that about?" Nate asked

"2 o'clock," Chick replied, eyes focused, as he nodded in the direction of the entrance to the penthouse, "looks like there is some new talent."

There came a girl stepping out of the lift. Nate was pretty sure she was a freshman, he'd seen her amongst the fresh batch of minions Blair had attained as soon as the school year had started. He'd thought she was quite pretty initially, then she'd looked up at him with that adoring look that most of the keen fresher girls seemed to give him and the attraction had ended there, there was only so much desperation he could take. His best friend, on the hand, was much less picky.

"Freshman," he stated.

"Perfect," Chuck said smirking, as he downed his glass of scotch.

"You are despicable," Nate chuckled

Straightening his bow tie, Chuck replied, "Hey, not all of can be freaking monks. I guarantee once you seal the deal with Virgin Mary, you'll understand," before walking away

Nate could only shake his head as he watched friend begin to zone in on his target, "Seal the deal? Who says that anymore?"

Turning back around to face Nate, Chuck raised his arms and shrugging says cockily, "Guys who are about to get laid." With a wink, he resumed his journey through the crowd.


End file.
